反应详情

温度

-78 °C

To a suspension of 7-chloroquinolin-2-yl-methyltriphenylphosphonium bromide (Example 4, Step 2) (809 mg, 1.56 mmol.) in THF (15 mL) at -78° C., was added a soltuion of n-BuLi (1.6M) in hexane (0.89 mL, 1.43 mmol.). The mixture was stirred for 0.5 hrs at -78° C. Then, (+)-methyl 5-(3-formylphenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (step 3) (480 mg, 1.3 mmol.) in THF (4 mL) was slowly added. The mixture was stirred for 0.5 hr at -78° C. and then warmed up to room temperature and stirred for an additional 2 hrs. A solution of 25% ammonium acetate was added, the mixture was extracted with ethyl acetate, and the extracts were washed with brine (3×), dried over sodium sulfate, filtered and evaporated to dryness. Purification by flash chromatography afforded the title compound.

1. stirringThe mixture was stirred for 0.5 hr at -78° C.
2. temperaturewarmed up to room temperature
3. stirringstirred for an additional 2 hrs
4. extractionthe mixture was extracted with ethyl acetate
5. washthe extracts were washed with brine (3×)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated to dryness
9. customPurification by flash chromatography